Galactonolactone (BioDeep_00000014470)

 

Secondary id: BioDeep_00001868630

human metabolite Endogenous


代谢物信息卡片


(3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one

化学式: C6H10O6 (178.04773600000001)
中文名称: 半乳糖酸內酯
谱图信息: 最多检出来源 Homo sapiens(blood) 2.18%

分子结构信息

SMILES: C(C(C1C(C(C(=O)O1)O)O)O)O
InChI: InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3-,4-,5+/m1/s1

描述信息

Galactonolactone has been determined in human urine by reversed-phase HPLC for the specific evaluation of metabolic by-products in the urine of galactosemic patients and based on the simultaneous determination of gluconolactone, galactonolactone and galactitol. (PMID: 1797843). Patients with galactose-1-phosphate uridyltransferase (GALT) deficiency, given a load of galactose have been shown to excrete six times as much galactonate in their urine as normal subjects exposed to the same experimental conditions. The production of galactonate occurs through the activity of a soluble NAD+-dependent galactose dehydrogenase, catalyzing the conversion of galactose to D-galactonolactone (D-galactose: NAD+ oxidoreductase, EC 1.1.1.48). (OMMBID).
Galactonolactone has been determined in human urine by reversed-phase HPLC for the specific evaluation of metabolic by-products in the urine of galactosemic patients and based on the simultaneous determination of gluconolactone, galactonolactone and galactitol. (PMID: 1797843)

同义名列表

15 个代谢物同义名

(3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one; gamma-delta-Galactonolactone; Galactonolactone, (D)-isomer; Galactonolactone, (L)-isomer; delta-galactono-1,4-Lactone; delta-galactono-1,5-Lactone; delta-galactono-8-Lactone; gamma-D-Galactonolactone; D-galactono-1,4-lactone; D-galactono-1,5-Lactone; delta-Galactonolactone; D-Glucono-1,4-lactone; D-galactono-8-Lactone; D-Galactonolactone; Galactonolactone



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Andrey A Chudin, Elena V Kudryashova. Impact of Lipid Matrix Composition on Activity of Membranotropic Enzymes Galactonolactone Oxidase from Trypanosoma cruzi and L-Galactono-1,4-Lactone Dehydrogenase from Arabidopsis thaliana in the System of Reverse Micelles. Biochemistry. Biokhimiia. 2023 Dec; 88(12):2073-2083. doi: 10.1134/s0006297923120106. [PMID: 38462451]
  • Andrey A Chudin, Igor D Zlotnikov, Sergey S Krylov, Victor V Semenov, Elena V Kudryashova. Allylpolyalkoxybenzene Inhibitors of Galactonolactone Oxidase from Trypanosoma cruzi. Biochemistry. Biokhimiia. 2023 Jan; 88(1):131-141. doi: 10.1134/s000629792301011x. [PMID: 37068875]
  • A Paradiso, M C de Pinto, V Locato, L De Gara. Galactone-γ-lactone-dependent ascorbate biosynthesis alters wheat kernel maturation. Plant biology (Stuttgart, Germany). 2012 Jul; 14(4):652-8. doi: 10.1111/j.1438-8677.2011.00543.x. [PMID: 22300256]
  • Peter Schertl, Stephanie Sunderhaus, Jennifer Klodmann, Gustavo E Gergoff Grozeff, Carlos G Bartoli, Hans-Peter Braun. L-galactono-1,4-lactone dehydrogenase (GLDH) forms part of three subcomplexes of mitochondrial complex I in Arabidopsis thaliana. The Journal of biological chemistry. 2012 Apr; 287(18):14412-9. doi: 10.1074/jbc.m111.305144. [PMID: 22378782]
  • Yongshun Gao, Adebanjo A Badejo, Yoshihiro Sawa, Takahiro Ishikawa. Analysis of two L-Galactono-1,4-lactone-responsive genes with complementary expression during the development of Arabidopsis thaliana. Plant & cell physiology. 2012 Mar; 53(3):592-601. doi: 10.1093/pcp/pcs014. [PMID: 22323769]
  • Macarena Mellado, Rodrigo A Contreras, Alberto González, Geraldine Dennett, Alejandra Moenne. Copper-induced synthesis of ascorbate, glutathione and phytochelatins in the marine alga Ulva compressa (Chlorophyta). Plant physiology and biochemistry : PPB. 2012 Feb; 51(?):102-8. doi: 10.1016/j.plaphy.2011.10.007. [PMID: 22153245]
  • Linda Mastropasqua, Giuseppe Borraccino, Laura Bianco, Costantino Paciolla. Light qualities and dose influence ascorbate pool size in detached oat leaves. Plant science : an international journal of experimental plant biology. 2012 Feb; 183(?):57-64. doi: 10.1016/j.plantsci.2011.11.009. [PMID: 22195578]
  • Mohammad Alimohammadi, Kanishka de Silva, Clarisse Ballu, Nawab Ali, Mariya V Khodakovskaya. Reduction of inositol (1,4,5)-trisphosphate affects the overall phosphoinositol pathway and leads to modifications in light signalling and secondary metabolism in tomato plants. Journal of experimental botany. 2012 Jan; 63(2):825-35. doi: 10.1093/jxb/err306. [PMID: 21994174]
  • András Szarka, Bálint Tomasskovics, Gábor Bánhegyi. The ascorbate-glutathione-α-tocopherol triad in abiotic stress response. International journal of molecular sciences. 2012; 13(4):4458-4483. doi: 10.3390/ijms13044458. [PMID: 22605990]
  • Liezel M Gouws, Eileen Botes, Anna J Wiese, Sandra Trenkamp, Ivone Torres-Jerez, Yuhong Tang, Paul N Hills, Björn Usadel, James R Lloyd, Alisdair R Fernie, Jens Kossmann, Margaretha J van der Merwe. The plant growth promoting substance, lumichrome, mimics starch, and ethylene-associated symbiotic responses in lotus and tomato roots. Frontiers in plant science. 2012; 3(?):120. doi: 10.3389/fpls.2012.00120. [PMID: 22701462]
  • Jason W Holder, Jil C Ulrich, Anthony C DeBono, Paul A Godfrey, Christopher A Desjardins, Jeremy Zucker, Qiandong Zeng, Alex L B Leach, Ion Ghiviriga, Christine Dancel, Thomas Abeel, Dirk Gevers, Chinnappa D Kodira, Brian Desany, Jason P Affourtit, Bruce W Birren, Anthony J Sinskey. Comparative and functional genomics of Rhodococcus opacus PD630 for biofuels development. PLoS genetics. 2011 Sep; 7(9):e1002219. doi: 10.1371/journal.pgen.1002219. [PMID: 21931557]
  • Laura Zsigmond, Bálint Tomasskovics, Veronika Deák, Gábor Rigó, László Szabados, Gábor Bánhegyi, András Szarka. Enhanced activity of galactono-1,4-lactone dehydrogenase and ascorbate-glutathione cycle in mitochondria from complex III deficient Arabidopsis. Plant physiology and biochemistry : PPB. 2011 Aug; 49(8):809-15. doi: 10.1016/j.plaphy.2011.04.013. [PMID: 21601466]
  • Saikrishna Talla, Khateef Riazunnisa, Lolla Padmavathi, Bobba Sunil, Pidakala Rajsheel, Agepati S Raghavendra. Ascorbic acid is a key participant during the interactions between chloroplasts and mitochondria to optimize photosynthesis and protect against photoinhibition. Journal of biosciences. 2011 Mar; 36(1):163-73. doi: 10.1007/s12038-011-9000-x. [PMID: 21451257]
  • Bernd Zechmann, M Stumpe, F Mauch. Immunocytochemical determination of the subcellular distribution of ascorbate in plants. Planta. 2011 Jan; 233(1):1-12. doi: 10.1007/s00425-010-1275-x. [PMID: 20872269]
  • Tiago Tomaz, Matthieu Bagard, Itsara Pracharoenwattana, Pernilla Lindén, Chun Pong Lee, Adam J Carroll, Elke Ströher, Steven M Smith, Per Gardeström, A Harvey Millar. Mitochondrial malate dehydrogenase lowers leaf respiration and alters photorespiration and plant growth in Arabidopsis. Plant physiology. 2010 Nov; 154(3):1143-57. doi: 10.1104/pp.110.161612. [PMID: 20876337]
  • Mingjun Li, Fengwang Ma, Chunmiao Guo, Jun Liu. Ascorbic acid formation and profiling of genes expressed in its synthesis and recycling in apple leaves of different ages. Plant physiology and biochemistry : PPB. 2010 Apr; 48(4):216-24. doi: 10.1016/j.plaphy.2010.01.015. [PMID: 20159657]
  • Vanessa J Melino, Kathleen L Soole, Christopher M Ford. Ascorbate metabolism and the developmental demand for tartaric and oxalic acids in ripening grape berries. BMC plant biology. 2009 Dec; 9(?):145. doi: 10.1186/1471-2229-9-145. [PMID: 19995454]
  • Virginie Garcia, Rebecca Stevens, Laurent Gil, Louise Gilbert, Noé Gest, Johann Petit, Mireille Faurobert, Mickael Maucourt, Catherine Deborde, Annick Moing, Jean-Luc Poessel, Daniel Jacob, Jean-Paul Bouchet, Jean-Luc Giraudel, Barbara Gouble, David Page, Moftah Alhagdow, Capucine Massot, Hélène Gautier, Martine Lemaire-Chamley, Antoine de Daruvar, Dominique Rolin, Bjoern Usadel, Marc Lahaye, Mathilde Causse, Pierre Baldet, Christophe Rothan. An integrative genomics approach for deciphering the complex interactions between ascorbate metabolism and fruit growth and composition in tomato. Comptes rendus biologies. 2009 Nov; 332(11):1007-21. doi: 10.1016/j.crvi.2009.09.013. [PMID: 19909923]
  • Nicole G H Leferink, Esther van Duijn, Arjan Barendregt, Albert J R Heck, Willem J H van Berkel. Galactonolactone dehydrogenase requires a redox-sensitive thiol for optimal production of vitamin C. Plant physiology. 2009 Jun; 150(2):596-605. doi: 10.1104/pp.109.136929. [PMID: 19369590]
  • Mingjun Li, Fengwang Ma, Peifen Shang, Min Zhang, Changming Hou, Dong Liang. Influence of light on ascorbate formation and metabolism in apple fruits. Planta. 2009 Jun; 230(1):39-51. doi: 10.1007/s00425-009-0925-3. [PMID: 19337748]
  • Tsuyoshi Imai, Yusuke Ban, Shingo Terakami, Toshiya Yamamoto, Takaya Moriguchi. L-Ascorbate biosynthesis in peach: cloning of six L-galactose pathway-related genes and their expression during peach fruit development. Physiologia plantarum. 2009 Jun; 136(2):139-49. doi: 10.1111/j.1399-3054.2009.01213.x. [PMID: 19453508]
  • Sean M Bulley, Maysoon Rassam, Dana Hoser, Wolfgang Otto, Nicole Schünemann, Michele Wright, Elspeth MacRae, Andrew Gleave, William Laing. Gene expression studies in kiwifruit and gene over-expression in Arabidopsis indicates that GDP-L-galactose guanyltransferase is a major control point of vitamin C biosynthesis. Journal of experimental botany. 2009; 60(3):765-78. doi: 10.1093/jxb/ern327. [PMID: 19129165]
  • Bernard Pineau, Ouardia Layoune, Antoine Danon, Rosine De Paepe. L-galactono-1,4-lactone dehydrogenase is required for the accumulation of plant respiratory complex I. The Journal of biological chemistry. 2008 Nov; 283(47):32500-5. doi: 10.1074/jbc.m805320200. [PMID: 18799460]
  • Yukinori Yabuta, Takanori Maruta, Ayana Nakamura, Takahiro Mieda, Kazuya Yoshimura, Takahiro Ishikawa, Shigeru Shigeoka. Conversion of L-galactono-1,4-lactone to L-ascorbate is regulated by the photosynthetic electron transport chain in Arabidopsis. Bioscience, biotechnology, and biochemistry. 2008 Oct; 72(10):2598-607. doi: 10.1271/bbb.80284. [PMID: 18838812]
  • Mario Houde, Amadou Oury Diallo. Identification of genes and pathways associated with aluminum stress and tolerance using transcriptome profiling of wheat near-isogenic lines. BMC genomics. 2008 Aug; 9(?):400. doi: 10.1186/1471-2164-9-400. [PMID: 18752686]
  • Ana Zabalza, Loli Gálvez, Daniel Marino, Mercedes Royuela, Cesar Arrese-Igor, Esther M González. The application of ascorbate or its immediate precursor, galactono-1,4-lactone, does not affect the response of nitrogen-fixing pea nodules to water stress. Journal of plant physiology. 2008 May; 165(8):805-12. doi: 10.1016/j.jplph.2007.08.005. [PMID: 17931744]
  • Annalisa Paradiso, Rosalia Berardino, Maria C de Pinto, Luigi Sanità di Toppi, Maria M Storelli, Franca Tommasi, Laura De Gara. Increase in ascorbate-glutathione metabolism as local and precocious systemic responses induced by cadmium in durum wheat plants. Plant & cell physiology. 2008 Mar; 49(3):362-74. doi: 10.1093/pcp/pcn013. [PMID: 18234716]
  • Jorge Loscos, Manuel A Matamoros, Manuel Becana. Ascorbate and homoglutathione metabolism in common bean nodules under stress conditions and during natural senescence. Plant physiology. 2008 Mar; 146(3):1282-92. doi: 10.1104/pp.107.114066. [PMID: 18218966]
  • Moftah Alhagdow, Fabien Mounet, Louise Gilbert, Adriano Nunes-Nesi, Virginie Garcia, Daniel Just, Johann Petit, Bertrand Beauvoit, Alisdair R Fernie, Christophe Rothan, Pierre Baldet. Silencing of the mitochondrial ascorbate synthesizing enzyme L-galactono-1,4-lactone dehydrogenase affects plant and fruit development in tomato. Plant physiology. 2007 Dec; 145(4):1408-22. doi: 10.1104/pp.107.106500. [PMID: 17921340]
  • Claudio Stasolla, Edward C Yeung. Cellular ascorbic acid regulates the activity of major peroxidases in the apical poles of germinating white spruce (Picea glauca) somatic embryos. Plant physiology and biochemistry : PPB. 2007 Mar; 45(3-4):188-98. doi: 10.1016/j.plaphy.2007.02.007. [PMID: 17400467]
  • Daniela Valenti, Rosa Anna Vacca, Maria Concetta de Pinto, Laura De Gara, Ersilia Marra, Salvatore Passarella. In the early phase of programmed cell death in Tobacco Bright Yellow 2 cells the mitochondrial adenine nucleotide translocator, adenylate kinase and nucleoside diphosphate kinase are impaired in a reactive oxygen species-dependent manner. Biochimica et biophysica acta. 2007 Jan; 1767(1):66-78. doi: 10.1016/j.bbabio.2006.11.004. [PMID: 17184729]
  • A D Attolico, M C De Tullio. Increased ascorbate content delays flowering in long-day grown Arabidopsis thaliana (L.) Heynh. Plant physiology and biochemistry : PPB. 2006 Jul; 44(7-9):462-6. doi: 10.1016/j.plaphy.2006.08.002. [PMID: 17023170]
  • Manuel A Matamoros, Jorge Loscos, Maria J Coronado, Javier Ramos, Shusei Sato, Pilar S Testillano, Satoshi Tabata, Manuel Becana. Biosynthesis of ascorbic acid in legume root nodules. Plant physiology. 2006 Jul; 141(3):1068-77. doi: 10.1104/pp.106.081463. [PMID: 16766673]
  • Zhenfei Guo, Huoquan Tan, Zhihui Zhu, Shaoyun Lu, Biyan Zhou. Effect of intermediates on ascorbic acid and oxalate biosynthesis of rice and in relation to its stress resistance. Plant physiology and biochemistry : PPB. 2005 Oct; 43(10-11):955-62. doi: 10.1016/j.plaphy.2005.08.007. [PMID: 16310370]
  • Takaaki Tokunaga, Katsunori Miyahara, Kazufumi Tabata, Muneharu Esaka. Generation and properties of ascorbic acid-overproducing transgenic tobacco cells expressing sense RNA for l-galactono-1,4-lactone dehydrogenase. Planta. 2005 Apr; 220(6):854-63. doi: 10.1007/s00425-004-1406-3. [PMID: 15549373]
  • María del Carmen Córdoba-Pedregosa, José Manuel Villalba, Francisco Córdoba, José Antonio González-Reyes. Changes in intracellular and apoplastic peroxidase activity, ascorbate redox status, and root elongation induced by enhanced ascorbate content in Allium cepa L. Journal of experimental botany. 2005 Feb; 56(412):685-94. doi: 10.1093/jxb/eri051. [PMID: 15582927]
  • Rosalia Liso, Mario C De Tullio, Samantha Ciraci, Raffaella Balestrini, Nicoletta La Rocca, Leonardo Bruno, Adriana Chiappetta, Maria Beatrice Bitonti, Paola Bonfante, Oreste Arrigoni. Localization of ascorbic acid, ascorbic acid oxidase, and glutathione in roots of Cucurbita maxima L. Journal of experimental botany. 2004 Dec; 55(408):2589-97. doi: 10.1093/jxb/erh262. [PMID: 15520029]
  • Luigi Tedone, Robert D Hancock, Salvatore Alberino, Sophie Haupt, Roberto Viola. Long-distance transport of L-ascorbic acid in potato. BMC plant biology. 2004 Sep; 4(?):16. doi: 10.1186/1471-2229-4-16. [PMID: 15377389]
  • Irene Pateraki, Maite Sanmartin, Mary S Kalamaki, Dimitrios Gerasopoulos, Angelos K Kanellis. Molecular characterization and expression studies during melon fruit development and ripening of L-galactono-1,4-lactone dehydrogenase. Journal of experimental botany. 2004 Aug; 55(403):1623-33. doi: 10.1093/jxb/erh186. [PMID: 15234991]
  • Elzbieta Kuzniak, Maria Skłodowska. The effect of Botrytis cinerea infection on the antioxidant profile of mitochondria from tomato leaves. Journal of experimental botany. 2004 Mar; 55(397):605-12. doi: 10.1093/jxb/erh076. [PMID: 14966215]
  • A Harvey Millar, Valentina Mittova, Guy Kiddle, Joshua L Heazlewood, Carlos G Bartoli, Frederica L Theodoulou, Christine H Foyer. Control of ascorbate synthesis by respiration and its implications for stress responses. Plant physiology. 2003 Oct; 133(2):443-7. doi: 10.1104/pp.103.028399. [PMID: 14555771]
  • Juan Antonio Tudela, José Antonio Hernández, María Isabel Gil, Juan Carlos Espín. L-galactono-gamma-lactone dehydrogenase aand vitamin C content in fresh-cut potatoes stored under controlled atmospheres. Journal of agricultural and food chemistry. 2003 Jul; 51(15):4296-302. doi: 10.1021/jf030071s. [PMID: 12848501]
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